Diisopropylethylamine → HCID 178418888、化合物

A solution of 5-benzoyl-2-chloromethylbenzimidazole (284 mg, 1.05 mmol), N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (476 mg, 1.04 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.08 mmol) were stirred at 80□ C in DMF (4 mL) for 16 hours. The reaction was then cooled, concentrated under reduced pressure and diluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL). The phases were separated and the aqueous phase was washed with CH2Cl2 (2×25 mL). The combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL), dried (NaSO4), filtered and concentrated under reduced pressure. Purification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH) provided the desired alkylated product (468 mg, 65%) as an orange oil.

1. temperatureThe reaction was then cooled
2. concentrationconcentrated under reduced pressure
3. additiondiluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL)
4. customThe phases were separated
5. washthe aqueous phase was washed with CH2Cl2 (2×25 mL)
6. washThe combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL)
7. dry with materialdried (NaSO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customPurification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH)

ORDレコード

ord-c3e65d3523c4435f91103dac99cfb3aa

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07084155B2